Originally from Geelong, Leith moved to Carlton in 1891 and then Melbourne in May 1896. He had originally sought a clearance to Essendon but it wasn't granted. A leading advocate of the place kick he once nailed five from five against St Kilda with the method and was four times Melbourne's leading goalkicker.

Almost ever present in the early years of Melbourne's life in the VFL, the one game he missed in 1898 was due to his child tragically passing away on the morning of a match. He returned the next week and played out the season but was well down on his form from the previous year.

Leith retired at the end of 1908 and worked as a trainer for the club but was persuaded to return in 1911 when he played as a defender in four games over two years before giving up the game for good just before his 40th birthday. At 39 years and 296 days is the second oldest man ever to have played VFL/AFL football, behind only Vic Cumberland

After his retirement Leith was a ground attendant at the MCG, and for many years operated the scoreboard. He was posthumously awarded life membership in 2005.